tert-butyl (3R)-3-aminopiperidine-1-carboxylate → HCID 25253063, compound

HRID 914061Notes

Reaction equation

HRID 914061 reaction equation
[CH:1]1([N:6]2[CH2:12][C:11]([F:14])([F:13])[C:10](=[O:15])[N:9]([CH3:16])[C:8]3[CH:17]=[N:18][C:19]([NH:21][C:22]4[CH:30]=[CH:29][C:25]([C:26]([OH:28])=O)=[CH:24][C:23]=4[O:31][CH3:32])=[N:20][C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1.CN(C(ON1N=[N:48][C:43]2[CH:44]=[CH:45][CH:46]=[N:47][C:42]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.N[C@@H]1CCCN(C(OC(C)(C)C)=O)C1>>[CH:1]1([N:6]2[CH2:12][C:11]([F:13])([F:14])[C:10](=[O:15])[N:9]([CH3:16])[C:8]3[CH:17]=[N:18][C:19]([NH:21][C:22]4[CH:30]=[CH:29][C:25]([C:26]([NH:48][C@@H:43]5[CH2:44][CH2:45][CH2:46][NH:47][CH2:42]5)=[O:28])=[CH:24][C:23]=4[O:31][CH3:32])=[N:20][C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 1501974tert-butyl (3R)-3-aminopiperidine-1-carboxylateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 252529054-(9-Cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[5,4-b][1,4]diazepin-2-ylamino)-3-methoxybenzoic acid

Product 1

HCID 25253063HCID 25253063, compound

Procedure

The title compound was synthesized from 4-(9-Cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[5,4-b][1,4]diazepin-2-ylamino)-3-methoxybenzoic acid as described in the General procedure for amide bond synthesis using HATU and (R)-tert-butyl 3-aminopiperidine-1-carboxylate, where Boc was removed using TFA in DCM. The final compound was purified by reverse phase HPLC and basified to give the free base. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.41-1.52 (m, 2H) 1.52-1.77 (m, 7H) 1.85-1.99 (m, 3H) 2.45 (t, J=9.9 Hz, 2H) 2.85 (d, J=12.4 Hz, 1H) 3.01 (dd, J=11.8, 3.4 Hz, 1H) 3.32 (s, 3H) 3.85 (m, 1H) 3.94 (s, 3H) 4.05 (t, J=14.0 Hz, 3H) 4.76 (quin, J=8.2 Hz, 1H) 7.47 (dd, J=1.8 Hz, 1H) 7.49 (s, 1H) 7.97 (s, 1H) 8.04 (d, J=7.8 Hz, 1H) 8.26 (s, 1H) 8.28 (d, 1H). [M+H] calc'd for C26H33F2N7O3, 530. found 530.

Workup

  1. customas described in the General procedure for amide bond synthesis
  2. customwas removed
  3. customThe final compound was purified by reverse phase HPLC
  4. customto give the free base

Sources & evidence

ORD record
ord-88b5e0d9ba004a21accad1250535b0dd
Source dataset
uspto-grants-2011_09
Patent number
US08026234B2

Reaction notes

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